diff --git a/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Inputs/main.c b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Inputs/main.c
--- a/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Inputs/main.c
+++ b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Inputs/main.c
@@ -1,8 +1,8 @@
-void stop() {}
+void relative();
 
 int main()
 {
-  stop();
-  // Hello World!
+  relative();
+  // Hello Absolute!
   return 0;
 }
diff --git a/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Inputs/relative.c b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Inputs/relative.c
new file mode 100644
--- /dev/null
+++ b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Inputs/relative.c
@@ -0,0 +1,5 @@
+void stop() {}
+void relative() {
+  stop();
+  // Hello Relative!
+}
diff --git a/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Makefile b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Makefile
--- a/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Makefile
+++ b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/Makefile
@@ -1,5 +1,10 @@
 BOTDIR = $(BUILDDIR)/buildbot
 USERDIR = $(BUILDDIR)/user
 C_SOURCES = $(BOTDIR)/main.c
+LD_EXTRAS = $(BOTDIR)/relative.o
 
 include Makefile.rules
+
+$(EXE): relative.o
+relative.o: $(BOTDIR)/relative.c
+	cd $(BOTDIR) && $(CC) -c $(CFLAGS) -o $@ relative.c
diff --git a/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/TestDSYMSourcePathRemapping.py b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/TestDSYMSourcePathRemapping.py
--- a/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/TestDSYMSourcePathRemapping.py
+++ b/lldb/packages/Python/lldbsuite/test/macosx/DBGSourcePathRemapping/TestDSYMSourcePathRemapping.py
@@ -17,7 +17,7 @@
         lldbutil.mkdir_p(botdir)
         lldbutil.mkdir_p(userdir)
         import shutil
-        for f in ['main.c']:
+        for f in ['main.c', 'relative.c']:
             shutil.copyfile(os.path.join(inputs, f), os.path.join(botdir, f))
             shutil.copyfile(os.path.join(inputs, f), os.path.join(userdir, f))
 
@@ -52,5 +52,10 @@
     @skipIf(debug_info=no_match("dsym"))
     def test(self):
         self.build()
-        lldbutil.run_to_name_breakpoint(self, 'main')
-        self.expect("source list", substrs=["Hello World"])
+        
+        target, process, _, _ = lldbutil.run_to_name_breakpoint(
+            self, 'main')
+        self.expect("source list -n main", substrs=["Hello Absolute"])
+        bkpt = target.BreakpointCreateByName('relative')
+        lldbutil.continue_to_breakpoint(process, bkpt)
+        self.expect("source list -n relative", substrs=["Hello Relative"])
diff --git a/lldb/source/Plugins/SymbolFile/DWARF/SymbolFileDWARF.cpp b/lldb/source/Plugins/SymbolFile/DWARF/SymbolFileDWARF.cpp
--- a/lldb/source/Plugins/SymbolFile/DWARF/SymbolFileDWARF.cpp
+++ b/lldb/source/Plugins/SymbolFile/DWARF/SymbolFileDWARF.cpp
@@ -179,6 +179,23 @@
   return *line_table;
 }
 
+static llvm::Optional<std::string>
+GetFileByIndex(const llvm::DWARFDebugLine::Prologue &prologue, size_t idx,
+               llvm::StringRef compile_dir, FileSpec::Style style) {
+  // Try to get an absolute path first.
+  std::string abs_path;
+  auto absolute = llvm::DILineInfoSpecifier::FileLineInfoKind::AbsoluteFilePath;
+  if (prologue.getFileNameByIndex(idx, compile_dir, absolute, abs_path, style))
+    return std::move(abs_path);
+
+  // Otherwise ask for a relative path.
+  std::string rel_path;
+  auto relative = llvm::DILineInfoSpecifier::FileLineInfoKind::Default;
+  if (!prologue.getFileNameByIndex(idx, compile_dir, relative, rel_path, style))
+    return {};
+  return std::move(rel_path);
+}
+
 static FileSpecList ParseSupportFilesFromPrologue(
     const lldb::ModuleSP &module,
     const llvm::DWARFDebugLine::Prologue &prologue, FileSpec::Style style,
@@ -188,27 +205,12 @@
 
   const size_t number_of_files = prologue.FileNames.size();
   for (size_t idx = 1; idx <= number_of_files; ++idx) {
-    std::string original_file;
-    if (!prologue.getFileNameByIndex(
-            idx, compile_dir,
-            llvm::DILineInfoSpecifier::FileLineInfoKind::Default, original_file,
-            style)) {
-      // Always add an entry so the indexes remain correct.
-      support_files.EmplaceBack();
-      continue;
-    }
-
     std::string remapped_file;
-    if (!prologue.getFileNameByIndex(
-            idx, compile_dir,
-            llvm::DILineInfoSpecifier::FileLineInfoKind::AbsoluteFilePath,
-            remapped_file, style)) {
-      // Always add an entry so the indexes remain correct.
-      support_files.EmplaceBack(original_file, style);
-      continue;
-    }
+    if (auto file_path = GetFileByIndex(prologue, idx, compile_dir, style))
+      if (!module->RemapSourceFile(llvm::StringRef(*file_path), remapped_file))
+        remapped_file = std::move(*file_path);
 
-    module->RemapSourceFile(llvm::StringRef(original_file), remapped_file);
+    // Unconditionally add an entry, so the indices match up.
     support_files.EmplaceBack(remapped_file, style);
   }